Tetramethylpyrazine

Tetramethylpyrazine
Names
	Preferred IUPAC name Tetramethylpyrazine
	Other names Ligustrazine; Tetrapyrazine
Identifiers
CAS Number	1124-11-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:133246;
ChemSpider	13658;
ECHA InfoCard	100.013.084
EC Number	214-391-2;
PubChem CID	14296;
UNII	V80F4IA5XG ;
CompTox Dashboard (EPA)	DTXSID6047070 ;
	InChI InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 Key: FINHMKGKINIASC-UHFFFAOYSA-N; InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 Key: FINHMKGKINIASC-UHFFFAOYSA-N;
	SMILES CC1=C(N=C(C(=N1)C)C)C;
Properties
Chemical formula	C8H12N2
Molar mass	136.198 g·mol−1
Melting point	84–86 °C (183–187 °F; 357–359 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans.^[1] In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter.^[2] When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate.^[3] It exhibits potential nootropic and antiinflammatory activities in rats.^[4]^[5]

References[]

^ Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi:10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2
^ Landis, Elizabeth A.; Oliverio, Angela M (January 26, 2021). "The diversity and function of sourdough starter microbiomes". eLife. 10: e61644. doi:10.7554/eLife.61644. Retrieved January 26, 2021.
^ Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 .doi:10.1038/1951103a0
^ Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D (2013). "Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway". Behavioural Brain Research. 253: 212–6. doi:10.1016/j.bbr.2013.07.052. PMID 23916742.
^ Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ (2013). "Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats". Experimental Neurology. 247: 188–201. doi:10.1016/j.expneurol.2013.04.010. PMID 23644042.

This article about a heterocyclic compound is a stub. You can help Wikipedia by .

[1] Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi:10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2

[2] Landis, Elizabeth A.; Oliverio, Angela M (January 26, 2021). "The diversity and function of sourdough starter microbiomes". eLife. 10: e61644. doi:10.7554/eLife.61644. Retrieved January 26, 2021.

[3] Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 .doi:10.1038/1951103a0

[4] Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D (2013). "Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway". Behavioural Brain Research. 253: 212–6. doi:10.1016/j.bbr.2013.07.052. PMID 23916742.

[Missingor-5] Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ (2013). "Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats". Experimental Neurology. 247: 188–201. doi:10.1016/j.expneurol.2013.04.010. PMID 23644042.

[1]

[2]

[3]

[4]

[5]